I travel a lot and I’m always looking to make the necessities easier so I can focus on those things that are unique on each trip. Getting the right bag to fit all my stuff is a big part of that. So I figured I should start talking about all of the bags I’ve gone through.

First, a few requirements that I have. I’m very picky about what I carry so my requirements are fairly strict. First, I want something I can put on my back or over my shoulder backpack style – roller bags are for dorks. Second, it’s got to fit in the overhead compartment and/or under the seat in front of me – checked bags are lost bags. Third, it’s got to be able to fit my basic outfits:

Two-piece suit – preferably without wrinkling it too much,

Two business shirts,

Two to Three undershirts,

A week’s worth of underwear,

A week’s worth of socks,

A pair of shoes,

Toiletries (inside a plastic bag in a convenient location), and

A t-shirt and pair of shorts/pants.

Those are the minimum things that I look for in a bag. Other niceties are things like someplace to put extra books, roller wheels (hey, sometimes my shoulder gets tired), internal structure, tie and belt compartments, lightweight, etc.

I took the Rick Steves’ Convertible Carry-On on my trip to Dallas. I’ve had it for a while but just didn’t put it to much use. So I pulled it out of the attic and opened it up. The bag is at the maximum allowable size for carry-on luggage by most airlines, which makes the interior cavernous. Also it expands a couple of inches. As far as carry-ons go, this is as big as you’re likely to find.

I put all of my stuff in it and still had room to spare. There was a good amount of room for my suit and business shirts and I locked them in with the internal straps so they wouldn’t go anywhere when I slung it on my back. Unfortunately everything else sagged to the bottom.

The bag is kind of lumpy and awkward. Even filling it up took effort as I had to lay it out, move it around, fit my clothes in, and move it around more. It’s like filling up a grocery sack – if you’ don’t just cram stuff in it’s not going to be pretty. And wearing it around felt funny. There’s just no structure to it or anything.

Pros:

Fits anything you’re likely to carry, short of a VW.

Extremely light and flexible

Cons:

Awkward when empty and uncomfortable to wear

Ugly

Conclusion: If it’s fully packed out, this bag is probably great. But nearly empty it’s just cumbersome. I’s built for trecking across the globe so that’s no surprise. The bag is very light so that’s also good for long hauls, especially in the Winter when you’ve got to pack lots of bulky stuff. But at that point you would probably be better off just grabbing a frame pack and going with that.

The TSA recently allowed you to leave your laptop in your bag to go through screening. But not just any bag qualifies. Basically, the bag has to allow the screener to see through the material without any cables or other things over it. There are lots of custom bags out that will do this. But here’s what I’ve used a couple of times: a plain siliconized shopping bag that you may get from clothing stores.

You can carry the “laptop bag” with you up to the screening point, then stow it in one of your carryon bags if you want. Or if you just want to have easy access to the laptop in your bag, the silicon seems to be easier for me to grip when sliding it out. For me this is a better process than buying a new bag just for ease of use.